Back to Search
Start Over
Synthesis of a C(4)–C(9) eleutheside template from d -glucal
- Source :
- Tetrahedron. 57:1183-1187
- Publication Year :
- 2001
- Publisher :
- Elsevier BV, 2001.
-
Abstract
- d -Glucal is converted to epoxy allylic alcohol 4 using an eight-step sequence that features a stereoselective methyl Grignard addition to an iodo-hexenulose. Epoxide formation via intramolecular iodide displacement occurs subsequent to an unusual hemiacetal reduction protocol involving LiBH4 in n-octanol. Alcohol 4 and the corresponding aldehyde (Z)-14 are potential C(4)–C(9) templates for eleutheside syntheses.
Details
- ISSN :
- 00404020
- Volume :
- 57
- Database :
- OpenAIRE
- Journal :
- Tetrahedron
- Accession number :
- edsair.doi...........a318df435ae207e505ee09e2f89cf71b
- Full Text :
- https://doi.org/10.1016/s0040-4020(00)01117-0